its startups Thoughts on the unique class of founders who call the Windy City home 16 cities. 6 months. Thousands of startups eager to change the world. That’s the 1776 Challenge Cup. And my fellowship is to document it, location by location, winner by winner. Chicago’s contest took place on Oct. 29, 2014. The Windy City, thankfully, held off on a lot of the wind…